JP2017501234A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017501234A5 JP2017501234A5 JP2016562079A JP2016562079A JP2017501234A5 JP 2017501234 A5 JP2017501234 A5 JP 2017501234A5 JP 2016562079 A JP2016562079 A JP 2016562079A JP 2016562079 A JP2016562079 A JP 2016562079A JP 2017501234 A5 JP2017501234 A5 JP 2017501234A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- pyridin
- acetamide
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 41
- 229910052739 hydrogen Inorganic materials 0.000 claims 29
- 239000001257 hydrogen Substances 0.000 claims 29
- -1 6-methyl-5- (4- (5- (2- (pyridin-2-yl) acetamido) -1,3,4-thiadiazol-2-yl) butyl) pyridin-2-yl Chemical group 0.000 claims 28
- 150000002431 hydrogen Chemical class 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000000304 alkynyl group Chemical group 0.000 claims 14
- 125000003342 alkenyl group Chemical group 0.000 claims 13
- 201000010099 disease Diseases 0.000 claims 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 12
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 8
- 239000011780 sodium chloride Substances 0.000 claims 8
- 125000005842 heteroatoms Chemical group 0.000 claims 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 7
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 5
- 150000001204 N-oxides Chemical class 0.000 claims 5
- 125000004429 atoms Chemical group 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 239000000651 prodrug Substances 0.000 claims 5
- 229940002612 prodrugs Drugs 0.000 claims 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 201000009673 liver disease Diseases 0.000 claims 4
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 4
- AJSXCYAUCOGGID-UHFFFAOYSA-N 2-[3-(trifluoromethoxy)phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(OC(F)(F)F)=C1 AJSXCYAUCOGGID-UHFFFAOYSA-N 0.000 claims 3
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 3
- 206010038428 Renal disease Diseases 0.000 claims 3
- 206010047115 Vasculitis Diseases 0.000 claims 3
- 230000001684 chronic Effects 0.000 claims 3
- 201000004624 dermatitis Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims 2
- YDHIMEXEGOCNHU-UHFFFAOYSA-N 2-pyridin-3-ylacetamide Chemical compound NC(=O)CC1=CC=CN=C1 YDHIMEXEGOCNHU-UHFFFAOYSA-N 0.000 claims 2
- 208000009094 Anemia, Hemolytic, Autoimmune Diseases 0.000 claims 2
- 206010003816 Autoimmune disease Diseases 0.000 claims 2
- 206010004661 Biliary cirrhosis primary Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000006454 Hepatitis Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 206010024324 Leukaemias Diseases 0.000 claims 2
- 206010025135 Lupus erythematosus Diseases 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010025310 Other lymphomas Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 201000005510 acute lymphocytic leukemia Diseases 0.000 claims 2
- 230000000202 analgesic Effects 0.000 claims 2
- 230000001387 anti-histamine Effects 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 239000000739 antihistaminic agent Substances 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 210000004027 cells Anatomy 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 231100000406 dermatitis Toxicity 0.000 claims 2
- 201000001981 dermatomyositis Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 201000005787 hematologic cancer Diseases 0.000 claims 2
- 231100000283 hepatitis Toxicity 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 2
- 239000003018 immunosuppressive agent Substances 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 200000000011 liver disorder Diseases 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- 201000002728 primary biliary cirrhosis Diseases 0.000 claims 2
- 201000004681 psoriasis Diseases 0.000 claims 2
- 150000003431 steroids Chemical class 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 1
- UXVCEKRAZBZVSL-UHFFFAOYSA-N 2-pyridin-2-ylacetamide Chemical compound NC(=O)CC1=CC=CC=N1 UXVCEKRAZBZVSL-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 229940035676 ANALGESICS Drugs 0.000 claims 1
- 229940116904 ANTIINFLAMMATORY THERAPEUTIC RADIOPHARMACEUTICALS Drugs 0.000 claims 1
- 206010000565 Acquired immunodeficiency syndrome Diseases 0.000 claims 1
- 206010000880 Acute myeloid leukaemia Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 210000004100 Adrenal Glands Anatomy 0.000 claims 1
- 208000002205 Allergic Conjunctivitis Diseases 0.000 claims 1
- 206010001897 Alzheimer's disease Diseases 0.000 claims 1
- 206010002026 Amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 206010002556 Ankylosing spondylitis Diseases 0.000 claims 1
- 108010047814 Antigen-Antibody Complex Proteins 0.000 claims 1
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 206010003246 Arthritis Diseases 0.000 claims 1
- 208000006673 Asthma Diseases 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 208000005783 Autoimmune Thyroiditis Diseases 0.000 claims 1
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims 1
- 206010050245 Autoimmune thrombocytopenia Diseases 0.000 claims 1
- 208000003950 B-Cell Lymphoma Diseases 0.000 claims 1
- 201000011497 Barrett's esophagus Diseases 0.000 claims 1
- 206010004161 Basedow's disease Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000003432 Bone Disease Diseases 0.000 claims 1
- 208000006386 Bone Resorption Diseases 0.000 claims 1
- 208000001183 Brain Injury Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000005846 Cardiomyopathy Diseases 0.000 claims 1
- 210000003169 Central Nervous System Anatomy 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010009887 Colitis Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 206010011005 Corneal dystrophy Diseases 0.000 claims 1
- 206010011401 Crohn's disease Diseases 0.000 claims 1
- 208000004275 Demyelinating Disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010012601 Diabetes mellitus Diseases 0.000 claims 1
- 208000005679 Eczema Diseases 0.000 claims 1
- 206010014612 Encephalitis viral Diseases 0.000 claims 1
- 206010014801 Endophthalmitis Diseases 0.000 claims 1
- XCKHWVUSVRTIFM-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1)CC(=O)NC1=CC=CC=N1)(F)F Chemical compound FC(OC=1C=C(C=CC=1)CC(=O)NC1=CC=CC=N1)(F)F XCKHWVUSVRTIFM-UHFFFAOYSA-N 0.000 claims 1
- 206010017758 Gastric cancer Diseases 0.000 claims 1
- 208000007565 Gingivitis Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 102000009127 Glutaminase Human genes 0.000 claims 1
- 108010073324 Glutaminase Proteins 0.000 claims 1
- 206010018651 Graft versus host disease Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
- 208000003807 Graves Disease Diseases 0.000 claims 1
- 201000004779 Graves' disease Diseases 0.000 claims 1
- 208000003579 Hashimoto's encephalitis Diseases 0.000 claims 1
- 206010019663 Hepatic failure Diseases 0.000 claims 1
- 208000007514 Herpes Zoster Diseases 0.000 claims 1
- 206010020243 Hodgkin's disease Diseases 0.000 claims 1
- 201000006743 Hodgkin's lymphoma Diseases 0.000 claims 1
- 201000001971 Huntington's disease Diseases 0.000 claims 1
- 208000009576 Hypercholesterolemia Diseases 0.000 claims 1
- 208000009326 Ileitis Diseases 0.000 claims 1
- 210000000987 Immune System Anatomy 0.000 claims 1
- 206010021972 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000005615 Interstitial Cystitis Diseases 0.000 claims 1
- 208000007766 Kaposi Sarcoma Diseases 0.000 claims 1
- 208000001083 Kidney Disease Diseases 0.000 claims 1
- 206010024229 Leprosy Diseases 0.000 claims 1
- 208000008456 Leukemia, Myelogenous, Chronic, BCR-ABL Positive Diseases 0.000 claims 1
- 208000007046 Leukemia, Myeloid, Acute Diseases 0.000 claims 1
- 208000007903 Liver Failure Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025650 Malignant melanoma Diseases 0.000 claims 1
- 206010028417 Myasthenia gravis Diseases 0.000 claims 1
- JVYIBLHBCPSTKF-UHFFFAOYSA-N N-pyridin-3-ylacetamide Chemical compound CC(=O)NC1=CC=CN=C1 JVYIBLHBCPSTKF-UHFFFAOYSA-N 0.000 claims 1
- 206010029151 Nephropathy Diseases 0.000 claims 1
- 208000009928 Nephrosis Diseases 0.000 claims 1
- 206010029164 Nephrotic syndrome Diseases 0.000 claims 1
- 206010061311 Nervous system neoplasm Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 206010029592 Non-Hodgkin's lymphomas Diseases 0.000 claims 1
- 229940074726 OPHTHALMOLOGIC ANTIINFLAMMATORY AGENTS Drugs 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 241000243985 Onchocerca volvulus Species 0.000 claims 1
- 208000002042 Onchocerciasis Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 208000008443 Pancreatic Carcinoma Diseases 0.000 claims 1
- 206010061536 Parkinson's disease Diseases 0.000 claims 1
- 210000001428 Peripheral Nervous System Anatomy 0.000 claims 1
- 206010034695 Pernicious anaemia Diseases 0.000 claims 1
- 208000005987 Polymyositis Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000005069 Pulmonary Fibrosis Diseases 0.000 claims 1
- 208000002098 Purpura, Thrombocytopenic, Idiopathic Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010039073 Rheumatoid arthritis Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 210000004116 Schwann Cells Anatomy 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 206010058141 Skin graft rejection Diseases 0.000 claims 1
- 208000000587 Small Cell Lung Carcinoma Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 208000008513 Spinal Cord Injury Diseases 0.000 claims 1
- 206010041823 Squamous cell carcinoma Diseases 0.000 claims 1
- 206010042742 Sympathetic ophthalmia Diseases 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 206010043207 Temporal arteritis Diseases 0.000 claims 1
- 206010043276 Teratoma Diseases 0.000 claims 1
- 210000001685 Thyroid Gland Anatomy 0.000 claims 1
- 206010043778 Thyroiditis Diseases 0.000 claims 1
- 206010044325 Trachoma Diseases 0.000 claims 1
- 241000390203 Trachoma Species 0.000 claims 1
- 210000002700 Urine Anatomy 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 206010046914 Vaginal infection Diseases 0.000 claims 1
- 206010047642 Vitiligo Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 230000000735 allogeneic Effects 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agents Drugs 0.000 claims 1
- 201000001320 atherosclerosis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 201000004982 autoimmune uveitis Diseases 0.000 claims 1
- 230000024279 bone resorption Effects 0.000 claims 1
- 201000008031 cardiomyopathy Diseases 0.000 claims 1
- 230000003197 catalytic Effects 0.000 claims 1
- 230000024881 catalytic activity Effects 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 201000006934 chronic myeloid leukemia Diseases 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 201000003883 cystic fibrosis Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 231100001003 eczema Toxicity 0.000 claims 1
- 201000002491 encephalomyelitis Diseases 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 201000008808 fibrosarcoma Diseases 0.000 claims 1
- 201000010175 gallbladder cancer Diseases 0.000 claims 1
- 201000010238 heart disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000000302 ischemic Effects 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 231100000835 liver failure Toxicity 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated Effects 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 201000009906 meningitis Diseases 0.000 claims 1
- 201000008806 mesenchymal cell neoplasm Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 201000003793 myelodysplastic syndrome Diseases 0.000 claims 1
- 201000002481 myositis Diseases 0.000 claims 1
- 231100001027 nephrosis Toxicity 0.000 claims 1
- 210000000653 nervous system Anatomy 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 210000000056 organs Anatomy 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 201000011152 pemphigus Diseases 0.000 claims 1
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 1
- 201000001245 periodontitis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 201000011461 pre-eclampsia Diseases 0.000 claims 1
- 230000002062 proliferating Effects 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 230000000306 recurrent Effects 0.000 claims 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims 1
- 201000010208 seminoma Diseases 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000010874 syndrome Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 201000006704 ulcerative colitis Diseases 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 201000008100 vaginitis Diseases 0.000 claims 1
- 201000002498 viral encephalitis Diseases 0.000 claims 1
- 201000006083 xeroderma pigmentosum Diseases 0.000 claims 1
- 0 C*1(C)C(*)=*C=*1 Chemical compound C*1(C)C(*)=*C=*1 0.000 description 14
- GVSNQMFKEPBIOY-UHFFFAOYSA-N Cc1c[nH]nn1 Chemical compound Cc1c[nH]nn1 GVSNQMFKEPBIOY-UHFFFAOYSA-N 0.000 description 2
- WVUHHPQQQLBMOE-UHFFFAOYSA-N Cc1cnc(C)[s]1 Chemical compound Cc1cnc(C)[s]1 WVUHHPQQQLBMOE-UHFFFAOYSA-N 0.000 description 2
- LCZUOKDVTBMCMX-UHFFFAOYSA-N Cc1cnc(C)cn1 Chemical compound Cc1cnc(C)cn1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 description 2
- ONIFNICATWBCHW-UHFFFAOYSA-N Cc1n[n](C)cn1 Chemical compound Cc1n[n](C)cn1 ONIFNICATWBCHW-UHFFFAOYSA-N 0.000 description 2
- XYYXDARQOHWBPO-UHFFFAOYSA-N Cc1nnc(C)[nH]1 Chemical compound Cc1nnc(C)[nH]1 XYYXDARQOHWBPO-UHFFFAOYSA-N 0.000 description 2
- GVBXHTCVVDWREE-UHFFFAOYSA-N Cc(ccc(C)n1)c1F Chemical compound Cc(ccc(C)n1)c1F GVBXHTCVVDWREE-UHFFFAOYSA-N 0.000 description 1
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N Cc1cnc(C)[nH]1 Chemical compound Cc1cnc(C)[nH]1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 1
- RHOOLJLEYYXKTK-UHFFFAOYSA-N Cc1cnc(C)nc1 Chemical compound Cc1cnc(C)nc1 RHOOLJLEYYXKTK-UHFFFAOYSA-N 0.000 description 1
- JXQGICFGPUAVLJ-UHFFFAOYSA-N Cc1nnc(C)[s]1 Chemical compound Cc1nnc(C)[s]1 JXQGICFGPUAVLJ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN36CH2014 | 2014-01-06 | ||
| IN36/CHE/2014 | 2014-01-06 | ||
| IN39CH2014 | 2014-01-06 | ||
| IN39/CHE/2014 | 2014-01-06 | ||
| IN2639CH2014 | 2014-05-29 | ||
| IN2647/CHE/2014 | 2014-05-29 | ||
| IN2647CH2014 | 2014-05-29 | ||
| IN2639/CHE/2014 | 2014-05-29 | ||
| IN2783/CHE/2014 | 2014-06-06 | ||
| IN2783CH2014 | 2014-06-06 | ||
| IN3525CH2014 | 2014-07-18 | ||
| IN3525/CHE/2014 | 2014-07-18 | ||
| IN3613CH2014 | 2014-07-24 | ||
| IN3613/CHE/2014 | 2014-07-24 | ||
| IN3612CH2014 | 2014-07-24 | ||
| IN3612/CHE/2014 | 2014-07-24 | ||
| IN5438CH2014 | 2014-10-31 | ||
| IN5438/CHE/2014 | 2014-10-31 | ||
| PCT/IB2015/050076 WO2015101958A2 (en) | 2014-01-06 | 2015-01-05 | Novel inhibitors of glutaminase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017501234A JP2017501234A (ja) | 2017-01-12 |
| JP2017501234A5 true JP2017501234A5 (da) | 2018-01-25 |
| JP6666263B2 JP6666263B2 (ja) | 2020-03-13 |
Family
ID=52478027
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016562079A Expired - Fee Related JP6666263B2 (ja) | 2014-01-06 | 2015-01-05 | グルタミナーゼの新規阻害剤 |
| JP2016562078A Active JP6783663B2 (ja) | 2014-01-06 | 2015-01-05 | 新規グルタミナーゼ阻害剤 |
| JP2019090711A Pending JP2019163290A (ja) | 2014-01-06 | 2019-05-13 | 新規グルタミナーゼ阻害剤 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016562078A Active JP6783663B2 (ja) | 2014-01-06 | 2015-01-05 | 新規グルタミナーゼ阻害剤 |
| JP2019090711A Pending JP2019163290A (ja) | 2014-01-06 | 2019-05-13 | 新規グルタミナーゼ阻害剤 |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US9783533B2 (da) |
| EP (2) | EP3092235A2 (da) |
| JP (3) | JP6666263B2 (da) |
| KR (3) | KR20220013017A (da) |
| CN (5) | CN112920180A (da) |
| AU (1) | AU2015204210B2 (da) |
| BR (1) | BR112016015706A8 (da) |
| CA (2) | CA2934702A1 (da) |
| CL (1) | CL2016001715A1 (da) |
| DK (1) | DK3092236T3 (da) |
| EA (3) | EA033163B1 (da) |
| ES (1) | ES2833576T3 (da) |
| IL (1) | IL246362B (da) |
| SG (1) | SG11201605478XA (da) |
| WO (2) | WO2015101958A2 (da) |
| ZA (1) | ZA201604272B (da) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2922832B1 (en) | 2012-11-21 | 2019-10-09 | Agios Pharmaceuticals, Inc. | Glutaminase inhibitors and methods of use |
| WO2014079011A1 (en) | 2012-11-22 | 2014-05-30 | Agios Pharmaceuticals, Inc. | Heterocyclic compounds for inhibiting glutaminase and their methods of use |
| EP3092235A2 (en) * | 2014-01-06 | 2016-11-16 | Rhizen Pharmaceuticals S.A. | Novel inhibitors of glutaminase |
| KR20160127149A (ko) * | 2014-03-21 | 2016-11-02 | 아지오스 파마슈티컬스 아이엔씨. | 화합물 및 이의 사용 방법 |
| MA49708A (fr) | 2014-04-30 | 2020-06-03 | Pfizer | Dérivés de dihétérocycle liés à cycloalkyle |
| HUE049600T2 (hu) | 2014-07-03 | 2020-10-28 | Univ Texas | GLS1 inhibitorok betegségek kezelésére |
| WO2016007647A1 (en) | 2014-07-09 | 2016-01-14 | The Johns Hopkins University | Glutaminase inhibitor discovery and nanoparticle-enhanced delivery for cancer therapy |
| EP3316887B1 (en) * | 2015-06-30 | 2020-04-08 | Board of Regents, The University of Texas System | Gls1 inhibitors for treating disease |
| WO2017023787A1 (en) * | 2015-07-31 | 2017-02-09 | The Johns Hopkins University | Methods and compositions for treating metabolic reprogramming disorders |
| US10842763B2 (en) | 2015-07-31 | 2020-11-24 | The Johns Hopkins University | Methods for cancer and immunotherapy using prodrugs of glutamine analogs |
| EA034571B1 (ru) | 2015-07-31 | 2020-02-21 | Дзе Джонс Хопкинс Юниверсити | Пролекарства аналогов глутамина |
| WO2017021177A1 (en) * | 2015-08-04 | 2017-02-09 | Universitat De Barcelona | Pharmaceutical combinations for use in the treatment of cancer |
| GB201520959D0 (en) | 2015-11-27 | 2016-01-13 | Astrazeneca Ab And Cancer Res Technology Ltd | Bis-pyridazine compounds and their use in treating cancer |
| TW201733587A (zh) * | 2015-11-30 | 2017-10-01 | 阿斯特捷利康公司 | 1,3,4-噻二唑化合物及其在治療癌症中之用途 |
| US10040789B2 (en) | 2015-11-30 | 2018-08-07 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| US9938265B2 (en) * | 2015-11-30 | 2018-04-10 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| WO2017109793A1 (en) * | 2015-12-21 | 2017-06-29 | Council Of Scientific & Industrial Research | Novel 1,2,3 triazole-thiazole compounds, process for preparation and use thereof |
| RU2018124266A (ru) | 2015-12-22 | 2020-01-23 | Боард Оф Реджентс, Де Юниверсити Оф Техас Систем | Солевые формы и полиморфы (R)-1-(4-(6-(2-(4-(3,3-дифторциклобутокси)-6-метилпиридин-2-ил)ацетамидо)пиридазин-3-ил)-2- фторбутил) -N-метил-1Н-1,2,3-триазол-4-карбоксамид |
| CN107474024B (zh) * | 2016-06-08 | 2022-12-13 | 北京赛林泰医药技术有限公司 | 一种谷氨酰酶抑制剂及其组合物和用途 |
| WO2018102715A1 (en) * | 2016-12-02 | 2018-06-07 | Indiana University Research And Technology Corporation | Compositions and methods for treating and/or reducing corneal dystrophy |
| WO2018228435A1 (zh) * | 2017-06-13 | 2018-12-20 | 南京明德新药研发股份有限公司 | 作为gls1抑制剂的化合物 |
| RU2020112558A (ru) | 2017-10-18 | 2021-11-18 | Боард Оф Регентс, Зе Юниверсити Оф Тексас Систем | Терапия на основе ингибитора глутаминазы |
| SI3700902T1 (sl) | 2017-10-27 | 2023-10-30 | Boehringer Ingelheim International Gmbh | Inhibitorji trpc6 |
| US20190269705A1 (en) * | 2017-11-27 | 2019-09-05 | Regents Of The University Of Minnesota | Methods and materials for treating graft versus host disease |
| CA3108158C (en) * | 2018-07-31 | 2023-05-16 | Eli Lilly And Company | 5-methyl-4-fluoro-thiazol-2-yl compounds |
| US20220119768A1 (en) * | 2018-11-08 | 2022-04-21 | The University Of Tokyo | Method for removing senescent cell, and method for preparing senescent cell |
| CN109223778B (zh) * | 2018-11-16 | 2021-07-27 | 上海市肺科医院 | C24h24n6o2s3在制备抗结核菌药物中的用途 |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| WO2020223267A1 (en) | 2019-05-01 | 2020-11-05 | Boehringer Ingelheim International Gmbh | (r)-(2-methyloxiran-2-yl)methyl 4-bromobenzenesulfonate |
| CN110746416A (zh) * | 2019-09-05 | 2020-02-04 | 中国药科大学 | 含有三氮唑结构的谷氨酰胺酶gls1抑制剂或其可药用的盐、其制备方法及用途 |
| AU2020417293A1 (en) | 2020-01-03 | 2022-09-01 | Berg Llc | Polycyclic amides as UBE2K modulators for treating cancer |
| CN111643669A (zh) * | 2020-06-30 | 2020-09-11 | 广东省中医院（广州中医药大学第二附属医院、广州中医药大学第二临床医学院、广东省中医药科学院） | 谷氨酰胺酶抑制剂在制备治疗银屑病的药物中的应用 |
| EP4355729A1 (en) | 2021-06-16 | 2024-04-24 | Celgene Corporation | Azetidinyl compounds comprising a carboxylic acid group for the treatment of neurodegenerative diseases |
| CN114805346A (zh) * | 2021-07-08 | 2022-07-29 | 成都硕德药业有限公司 | 杂环类衍生物、其制备方法及用途 |
| CN116023375A (zh) * | 2021-10-25 | 2023-04-28 | 成都苑东生物制药股份有限公司 | 一种杂环类衍生物、其制备方法及用途 |
| WO2023212718A2 (en) * | 2022-04-29 | 2023-11-02 | Cornell University | Methods of treating a virus infection and methods of inhibiting viral replication |
| CN114874186B (zh) * | 2022-05-16 | 2023-07-11 | 深圳大学 | 一种谷氨酰胺酰基环化酶同工酶抑制剂及其制备方法与应用 |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2104783A1 (en) * | 1970-07-14 | 1972-04-21 | Berlin Chemie Veb | 2,5-disubstd 2-amino-1,3,4-thiadiazoles-from 4-substd 1-acylthiosemic - virustatics |
| JPH0358980A (ja) * | 1989-07-28 | 1991-03-14 | Canon Inc | 液晶性化合物、これを含む液晶組成物、およびこれを使用した液晶素子 |
| EP0656210A1 (en) | 1993-11-19 | 1995-06-07 | Takeda Chemical Industries, Ltd. | Imidazole derivatives as glutaminose inhibitors |
| US6310093B1 (en) | 1997-08-29 | 2001-10-30 | Elan Pharmaceuticals, Inc. | Method of preventing neuronal death |
| AU4030200A (en) | 1999-04-02 | 2000-10-23 | Children's Hospital Of Los Angeles | Use of asparaginase and glutaminase to treat autoimmune disease and graft versushost disease |
| US6451828B1 (en) | 2000-08-10 | 2002-09-17 | Elan Pharmaceuticals, Inc. | Selective inhibition of glutaminase by bis-thiadiazoles |
| NO315152B1 (no) | 2001-06-28 | 2003-07-21 | Tomm Slater | Anordning for rensing av luft |
| EP1434576A4 (en) | 2001-09-13 | 2006-03-29 | Kenneth E Miller | METHOD FOR RELIEVING PAIN |
| SE0300456D0 (sv) * | 2003-02-19 | 2003-02-19 | Astrazeneca Ab | Novel compounds |
| EP1597256A1 (en) * | 2003-02-21 | 2005-11-23 | Pfizer Inc. | N-heterocyclyl-substituted amino-thiazole derivatives as protein kinase inhibitors |
| DE10326821A1 (de) | 2003-06-11 | 2005-01-05 | Medical Enzymes Ag | Pharmazeutische Kombinationspräparate zur Krebstherapie |
| US20060276438A1 (en) | 2004-10-04 | 2006-12-07 | Natarajan Sethuraman | Prevention and treatment of influenza with glutamine antagonist agents |
| JP4871289B2 (ja) * | 2005-10-06 | 2012-02-08 | 日本曹達株式会社 | 環状アミン化合物および有害生物防除剤 |
| JP2009536173A (ja) | 2006-05-10 | 2009-10-08 | メディカル エンザイムズ アクチエンゲゼルシャフト | グルタドン |
| TW200819437A (en) * | 2006-08-17 | 2008-05-01 | Astrazeneca Ab | Chemical compounds |
| US7638541B2 (en) * | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| CN101616586B (zh) * | 2006-12-28 | 2014-08-13 | 赛马拜制药公司 | 治疗糖尿病和代谢性病症的杂环受体激动剂 |
| CN101754962B (zh) | 2007-07-19 | 2013-12-25 | 赛马拜制药公司 | 作为rup3或gpr119受体的激动剂治疗糖尿病和代谢性病症的n-氮杂环状经取代吡咯、吡唑、咪唑、三唑和四唑衍生物 |
| EP2271619A1 (en) * | 2008-04-07 | 2011-01-12 | Irm Llc | Compounds and compositions as modulators of gpr119 activity |
| US20110112103A1 (en) * | 2008-04-22 | 2011-05-12 | Daiichi Sankyo Company, Limited | 5-hydroxypyrimidine-4-carboxamide compound |
| US20100041663A1 (en) * | 2008-07-18 | 2010-02-18 | Novartis Ag | Organic Compounds as Smo Inhibitors |
| JPWO2010013849A1 (ja) * | 2008-08-01 | 2012-01-12 | 日本ケミファ株式会社 | Ｇｐｒ１１９作動薬 |
| WO2010033871A2 (en) | 2008-09-18 | 2010-03-25 | The Johns Hopkins University | Compositions and methods targeting glutaminase |
| WO2010045303A2 (en) * | 2008-10-16 | 2010-04-22 | Schering Corporation | Pyrrolidine, piperidine and piperazine derivatives and methods of use thereof |
| WO2010048149A2 (en) * | 2008-10-20 | 2010-04-29 | Kalypsys, Inc. | Heterocyclic modulators of gpr119 for treatment of disease |
| JP2010138082A (ja) * | 2008-12-09 | 2010-06-24 | Nippon Soda Co Ltd | 環状アミン化合物またはその塩、並びに有害生物防除剤 |
| WO2010111504A2 (en) | 2009-03-25 | 2010-09-30 | Cornell University | Inhibition of glutaminase c |
| US20120245344A1 (en) | 2009-08-31 | 2012-09-27 | Nippon Chemiphar Co., Ltd. | Gpr119 agonist |
| CN105801550B (zh) * | 2009-11-05 | 2019-06-14 | 理森制药股份公司 | 新型苯并吡喃激酶调节剂 |
| ES2362770B1 (es) | 2009-12-24 | 2012-05-22 | Universidad De Sevilla | Uso de compuesto n-fenil-n'-(3-metil-2-butenil)tiourea para la elaboración de medicamentos destinados al tratamiento de la encefalopatía hepática. |
| CN102971304A (zh) * | 2010-02-01 | 2013-03-13 | 日本化学医药株式会社 | Gpr119激动剂 |
| US20130109643A1 (en) | 2010-05-10 | 2013-05-02 | The Johns Hopkins University | Metabolic inhibitor against tumors having an idh mutation |
| EP2571878B1 (en) * | 2010-05-17 | 2018-10-17 | Incozen Therapeutics Pvt. Ltd. | Novel 3,5-disubstitued-3h-imidazo[4,5-b]pyridine and 3,5- disubstitued -3h-[1,2,3]triazolo[4,5-b]pyridine compounds as modulators of protein kinases |
| US10064885B2 (en) | 2010-07-09 | 2018-09-04 | Massachusetts Institute Of Technology | Metabolic gene, enzyme, and flux targets for cancer therapy |
| WO2012034123A1 (en) | 2010-09-10 | 2012-03-15 | Cornell University | Activating phosphorylation site on glutaminase c |
| JP2014094886A (ja) * | 2011-02-28 | 2014-05-22 | Nippon Chemiphar Co Ltd | Ｇｐｒ１１９作動薬 |
| CN103030597B (zh) | 2011-09-30 | 2014-10-01 | 南昌滨西科技有限公司 | 肾脏型谷氨酰胺酶抑制剂及其制备方法和用途 |
| TW201321353A (zh) | 2011-10-08 | 2013-06-01 | Novartis Ag | 胺基甲酸酯／尿素衍生物 |
| SG10201607685SA (en) * | 2011-11-21 | 2016-11-29 | Calithera Biosciences Inc | Heterocyclic inhibitors of glutaminase |
| US8604016B2 (en) | 2011-11-21 | 2013-12-10 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| EP2895623B1 (en) | 2012-09-17 | 2018-08-22 | Agios Pharmaceuticals, Inc. | Use of e-cadherin and vimentin for selection of treatment responsive patients |
| SG11201503720SA (en) | 2012-11-16 | 2015-06-29 | Calithera Biosciences Inc | Heterocyclic glutaminase inhibitors |
| EP2922832B1 (en) | 2012-11-21 | 2019-10-09 | Agios Pharmaceuticals, Inc. | Glutaminase inhibitors and methods of use |
| US9029531B2 (en) | 2012-11-22 | 2015-05-12 | Agios Pharmaceuticals, Inc. | Compounds and their methods of use |
| WO2014079011A1 (en) * | 2012-11-22 | 2014-05-30 | Agios Pharmaceuticals, Inc. | Heterocyclic compounds for inhibiting glutaminase and their methods of use |
| WO2014089048A1 (en) | 2012-12-03 | 2014-06-12 | Calithera Biosciences, Inc. | Treatment of cancer with heterocyclic inhibitors of glutaminase |
| EP3092235A2 (en) * | 2014-01-06 | 2016-11-16 | Rhizen Pharmaceuticals S.A. | Novel inhibitors of glutaminase |
| MA49708A (fr) * | 2014-04-30 | 2020-06-03 | Pfizer | Dérivés de dihétérocycle liés à cycloalkyle |
-
2015
- 2015-01-05 EP EP15705095.6A patent/EP3092235A2/en not_active Withdrawn
- 2015-01-05 CN CN202110114920.6A patent/CN112920180A/zh active Pending
- 2015-01-05 CN CN201580009614.9A patent/CN106029659B/zh not_active Expired - Fee Related
- 2015-01-05 KR KR1020227001963A patent/KR20220013017A/ko not_active Application Discontinuation
- 2015-01-05 US US14/769,331 patent/US9783533B2/en active Active
- 2015-01-05 KR KR1020167021580A patent/KR20160100407A/ko not_active Application Discontinuation
- 2015-01-05 CA CA2934702A patent/CA2934702A1/en not_active Abandoned
- 2015-01-05 KR KR1020167021582A patent/KR20160100408A/ko not_active Application Discontinuation
- 2015-01-05 CN CN202010671865.6A patent/CN111892589A/zh active Pending
- 2015-01-05 EP EP15705845.4A patent/EP3092236B1/en active Active
- 2015-01-05 WO PCT/IB2015/050076 patent/WO2015101958A2/en active Application Filing
- 2015-01-05 EA EA201691135A patent/EA033163B1/ru unknown
- 2015-01-05 BR BR112016015706A patent/BR112016015706A8/pt not_active Application Discontinuation
- 2015-01-05 CN CN202010256915.4A patent/CN111393431A/zh active Pending
- 2015-01-05 CN CN201580006698.0A patent/CN105960405B/zh not_active Expired - Fee Related
- 2015-01-05 DK DK15705845.4T patent/DK3092236T3/da active
- 2015-01-05 WO PCT/IB2015/050075 patent/WO2015101957A2/en active Application Filing
- 2015-01-05 CA CA2934700A patent/CA2934700A1/en not_active Abandoned
- 2015-01-05 JP JP2016562079A patent/JP6666263B2/ja not_active Expired - Fee Related
- 2015-01-05 AU AU2015204210A patent/AU2015204210B2/en not_active Ceased
- 2015-01-05 US US14/769,365 patent/US20160297761A1/en not_active Abandoned
- 2015-01-05 ES ES15705845T patent/ES2833576T3/es active Active
- 2015-01-05 EA EA201691134A patent/EA035499B1/ru unknown
- 2015-01-05 EA EA201991183A patent/EA201991183A1/ru unknown
- 2015-01-05 SG SG11201605478XA patent/SG11201605478XA/en unknown
- 2015-01-05 JP JP2016562078A patent/JP6783663B2/ja active Active
-
2016
- 2016-06-21 IL IL246362A patent/IL246362B/en unknown
- 2016-06-23 ZA ZA2016/04272A patent/ZA201604272B/en unknown
- 2016-07-05 CL CL2016001715A patent/CL2016001715A1/es unknown
-
2017
- 2017-08-31 US US15/693,291 patent/US10611759B2/en not_active Expired - Fee Related
-
2019
- 2019-05-13 JP JP2019090711A patent/JP2019163290A/ja active Pending
-
2020
- 2020-03-20 US US16/825,755 patent/US20210032236A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017501234A5 (da) | ||
| JP2017505808A5 (da) | ||
| JP2019163290A5 (da) | ||
| CN111491918B (zh) | 芳基和杂芳基取代的吲哚化合物 | |
| JP2009524670A5 (da) | ||
| RU2018137194A (ru) | Ингибиторы бромдомена | |
| JP2016522246A5 (da) | ||
| HRP20171610T1 (hr) | Selektivni inhibitori pi3k delta | |
| JP2020537657A5 (da) | ||
| JP2017512786A5 (da) | ||
| JP2016526576A5 (da) | ||
| JP2016525078A5 (da) | ||
| JP2017532360A5 (da) | ||
| JP2016520131A5 (da) | ||
| JP2018510183A5 (da) | ||
| JP2018534326A5 (da) | ||
| JP2019503385A5 (da) | ||
| JP2010509342A5 (da) | ||
| JP2017510644A5 (da) | ||
| RU2014106020A (ru) | Ингибиторы втк | |
| JP2017510642A5 (da) | ||
| JP2010535218A5 (da) | ||
| JP2008531574A (ja) | Ｖｅｇｆ−ｒ２阻害剤としてのイミダゾ（１，２−ａ）ピリジン化合物 | |
| CA2930060A1 (en) | Alkyl-amide-substituted pyridyl compounds useful as modulators of il-12, il-23 and/or ifnalpha responses | |
| JP2017510643A5 (da) |